Reinventing Professionals

I spoke with Torben Rankine, the Director of Corporate Sales at SS&C Intralinks, following the company's 2nd Annual AI Bootcamp on Tuesday, May 19, 2026. We discussed how corporate development teams in Silicon Valley are identifying opportunities in the current market, applying generative and agentic AI to drive growth within their organizations, and aligning legal and deal-process teams.

I spoke with Kyle Robisch, a partner at Latitude Legal, a provider of flexible legal talent, and founder of its Tampa office. We discussed the value of flex legal talent, how AI is creating both headwinds and tailwinds for it, and how lawyers can position themselves to succeed in 2026.

In this 57th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the emergence of AI-first law firms, Claude for Legal, upskilling to advance your career, and verifying legal citations. 

I spoke with John Jakovenko, the founder of Jakovenko Group, a law firm consulting company focused on operational excellence, financial clarity, and scalable growth. We discussed the biggest operational blind spots facing small and midsize law firms, why firms struggle with profitability even when revenue looks strong, how law firms can implement KPIs, and the first system managing partners should fix.

I spoke with Adam Masarek, a lawyer, epidemiologist, and the Legal Marketing Manager for Lex Machina®, the LexisNexis® Legal Analytics® platform. We discussed how complex, high-stakes disputes are evolving, what the Trade Secret Litigation Report reveals about trade secret litigation, and the value of moving from intuition-based decisions to evidence-based planning in high-stakes cases.

I spoke with Tony McKenna, the Chief Information Officer at Lawfront, a group of regional law firms focused on providing legal services in the UK. We discussed how Lawfront differs from a traditional law firm, the advantages of law firms aligned with Lawfront that other independent firms may not have, and how AI is affecting the law firm business model.

I spoke with Matt Pollins, the Co-Founder and Chief Product Officer at Lupl, a work management platform for attorneys and agent teams. He is also the Co-Founder of Vibecode.law, an open community platform launched in 2026 for legal professionals to learn how to build apps and share what they’ve made. We discussed the value of combining attorneys with Agent Teams, the genesis of vibecode.law, and the value of vibecoding in legal.

I spoke with David Solomon and Joe Tiano, the CEO and Co-Founder, respectively, at Legal Decoder, a legal spend analytics platform. We discussed how Legal Decoder’s analytics approach differs from traditional e-billing review or timekeeper compliance tools, the company’s investment from Trajectory Capital, and how AI is changing the way legal work is structured, priced, and delivered.

I spoke with Vicente Silveira, the Co-Founder and CEO at AI Drive, a platform for legal professionals and teams to deploy agents that support document-intensive projects. We discussed the importance of trust and accuracy in AI-powered legal document analysis, the value of a multi-model approach, and where AI agents in legal work are headed.

In this 56th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the 10th Anniversary of the Lexpo Conference, best practices for assessing the value of legal AI investments, and the LexisNexis AI Symposium on May 5th in New York City.

I spoke with Bill Schroeder, the founder and co-principal of Clarity, a consultancy focused on brand research, brand strategy, and brand-driven change programs for law firms. We discussed how law firm branding is unique, the effect of brand-driven change programs, and branding advice for law firm managing partners.

I spoke with Nick Fleisher, the Co-Founder and CEO of Sandstone, an AI-native control tower for corporate legal departments. We discussed how Sandstone differs from Contract Lifecycle Management tools, the biggest challenges of introducing new technology in a corporate legal department, and how technology is transforming the way in-house legal teams operate.

I spoke with Nick West, a Partner and the Chief Strategy Officer at Mishcon de Reya. We discussed the firm's approach to innovation, the metrics it captures related to its use of Legora, how it measures the ROI of Legora and other tools, how law firms should think about the return on their technology investments, and the new Legora ROI Report.

In this 55th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed our impressions of Legalweek 2026, the ROI of legal AI, and the maturation of AI deployment in law firms and corporate legal departments.

I spoke with Pat Utz, the Co-Founder and CEO of Abstract, an AI policy intelligence platform for legislation and regulation. We discussed how Abstract sources its information, how customers use it to understand state and federal regulations, the unique type of intelligence it provides, and the importance of guardrails for relying on the output of AI-assisted technology.

I spoke with Alex Sappington, the Co-CEO of PageVault, a tool for capturing online content in a legally defensible manner. We discussed PageVault’s launch of Stencil, the problem Stencil solves for trademark teams, how PageVault’s work in litigation strengthens its role in trademarks, and where Stencil fits within the broader array of legal technology tools.

I spoke with Matt Basile, the CEO of Naya Software, a software company that automates the legal aspects of originating commercial real estate loans for law firms and institutional lenders. We discussed building a software company while working full-time as a lawyer, new ways law firms are leveraging artificial intelligence, and whether now is the best time to begin practicing law.

I spoke with Cristin Traylor, the Senior Director of AI Transformation and Law Firm Strategy at Relativity, a legal data intelligence company that builds technology to help users organize data, discover the truth, and act on it. We discussed the release of aiR for Case Strategy, how it compares with other AI solutions in legal, and how it will affect the day-to-day work of litigation professionals.